Sissy Training Stories

41,670 results
Orientation
Length
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Infinite Scroll

Mistress Commands Me in the Office Pt. 02

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Oh god, mistress, my dick is so hard in my panties now. At your command, in full view of the three vid-cams you made me install in my work cubicle, right here in the middle of my work day, with my associates working only feet away, on the other side of the cubical walls, you made me do it. Your commands, your training, your trigger words. My compliance. My s...

Lace and Love Ch. 03

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Jake Orlov grabbed his duffle bag and rifle case out of the cab of his F-250. He had some other gear in the truck, but he decided to get the rest later. He was exhausted from driving back from Kentucky, training the Blackwell county sheriff's department's SWAT team for the past week. Jake was disgusted at how these guys managed to graduate the police academ...

Mandy's Reward

by sissymaidrose on Sep 12, 2017
Transsexuals & Crossdressers

There was a sharp, heavy rap at the door. Mandy scrambled out of bed as Mistress Charlotte pushed the door open, hastily smoothing the tiny, soft, pink and green nightdress that barely went past her hips and surreptitiously tugged the matching knickers down from where they had ridden up into her bottom. As Mistress sashayed past to the throne like chair in t...

Feminizing First Step Ch. 05

by antares34 on Mar 30, 2020
Transgender & Crossdressers

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. Chapter 5 Today began like any other. I awoke in my bed with my wireless earbuds still in my ears. The sissy hypnosis audio track was gently playing...

Training Aide Ch. 03

by Angelscuck on Sep 14, 2017
BDSM

Just as the class started to break, one of the women said, "Great, I really need to pee!" "Wait a minute," Mistress Elaine announced. "We can use this as part of our training. It's called "Human Toilet". A plastic tarp was placed on the floor and I was positioned on top of it, on my back and ordered under punishment of canning, not to close my mouth. The w...

From Her Ex-Boss to her Bitch Pt. 03

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

This story contains extreme fantasies of Fem Domme, watersports, cock sucking, forced bi, if these aspects are likely to upset you please do not read on. ***** Pete had been taken in by Rachel, encouraged along the way, with a little titillation and confessions of her bisexuality. For a married man he had admitted too much and allowed himself to be taken f...

The Set Up Pt. 02

by undermythumb10 on Sep 15, 2017
Fetish

This is the continued story of my life as a sissy and is a continuation from part 1 The Set Up. ***** As I mentioned I am sat tied to a chair with my stepdaughters panties placed so the crutch is over my nose, it's a long story which started when I met and married my wife now Mistress some six months ago. I am now a total submissive sissy cum slut for my...

Always Read Before You Sign Ch. 02

by Reaver90 on Apr 6, 2020
Transgender & Crossdressers

Sam stood outside Miss Turner's front door. The weekend was hell was for him. He couldn't sleep, he had to sit down on the toilet and pee like a girl and more importantly, he couldn't jack off. The young man feared what the beautiful woman but deadly woman had in store for him. He took a heavy breath and knocked on the door. He waited for a few seconds as t...

Dinner Date with Mommy Pt. 04

by SissyStoryTime on Dec 3, 2018
Transgender & Crossdressers

Disclaimer - This story includes the following themes: Femdom, sissification, feminization, forced-bi, forced cum-eating, butt plugs, anal play, strap-ons, spanking, humiliation, CBT, chastity, and domestic servitude. If these themes do not interest you, then this story isn't for you, sweetheart. For everyone else... This is it. What you've waited for. Th...

Recruiting of a Sissy Maid Ch. 02

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Two: Onto Her Training and Breaking Down. The feeling of fear and dread falls over Chantel as she sits on the flimsy bed in what is for now her prison cell. Totally alone and isolated except for the fact that Mitch and Nate Burrows will lord over her as they orientate, train and ultimately break Chantel from a fantasy sissy to what will be a living...